Baeyer-Villiger-including domino two-step oxidations of β-O-substituted primary alcohols: Reflection of the migratory aptitudes of O-substituted alkyl group in the outcome of the reaction

Tom Targel, Moshe Portnoy

Research output: Contribution to journalArticlepeer-review

Abstract

Following the recent development of the one-pot two-step oxidation protocol for primary β-alkoxy alcohols, additional primary β-oxy alcohols were examined under similar conditions. The outcome of these reactions closely follows the migratory aptitudes of the related α-oxy-alkyls in Baeyer-Villiger oxidation vs. that of hydrogen. Thus, these experiments helped to establish the correct order of these aptitudes for α-oxy-alkyls. Furthermore, in the case of primary β,β-dialkoxyalcohols, the formation of dialkoxymethyl formates by the domino oxidation reaction was followed by secondary reactions, forming a number of interesting products.

Original languageEnglish
Article number1275
Pages (from-to)1-13
Number of pages13
JournalCatalysts
Volume10
Issue number11
DOIs
StatePublished - Nov 2020

Keywords

  • Domino reactions
  • Migratory aptitudes
  • Organocatalysis
  • Oxidations
  • Synthetic methods

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